1. Field of the Invention
The invention is a process for the preparation of cyclic-sulfur fluorine containing oxazolidinone antibacterial agents.
2. Description of the Related Art
Many processes are known for producing pharmaceutically antibacterial oxazolidinones, see for example, International Publication WO97/37980. However, when the the oxazolidinone contains an o-halogen substituted phenyl ring, decomposition of the metallated benzene to a reactive benzyne is a known undesirable side reaction, see "Dehydrobenzene and Cycloalkynes" by R. W. Hoffmann, Academic Press, N.Y., 1967. The process of the present invention produces a tetrahydrothiopyran-o-fluorinated oxazolidinones intermediate (IV) which is useful in producing antibacterially active oxazolidinones (XIV), (XIX) and N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1-oxido-2H-thiopyran4-yl)-phenyl]-2-oxo -5-oxazolidinyl]methyl]ethanethioamide.
International Publication WO97/09328 discloses tetrahydrothiopyran-o-fluorinated oxaxolidinones which are produced by a process which requires much colder temperatures, than the claimed invention.
International Publication WO97/30995 discloses tetrahydrothiopyran-o-fluorinated oxaxolidinones which are produced by a process different that that of the present invention